JP4913121B2 - Red phosphorescent compound and organic electroluminescent device using the same - Google Patents

Red phosphorescent compound and organic electroluminescent device using the same Download PDF

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JP4913121B2
JP4913121B2 JP2008500599A JP2008500599A JP4913121B2 JP 4913121 B2 JP4913121 B2 JP 4913121B2 JP 2008500599 A JP2008500599 A JP 2008500599A JP 2008500599 A JP2008500599 A JP 2008500599A JP 4913121 B2 JP4913121 B2 JP 4913121B2
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phosphorescent compound
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ユン クン キム，
チョン クン パク，
チョン デ ソ，
ヒュン チョル チョン，
キュン ホン リー，
サン テ パク，
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Description

本発明は有機電界発光装置に係り、さらに詳しくは、赤色リン光化合物及びこれを用いた有機電界発光装置に関する。より具体的に、本発明は、アノード、ホール注入層、ホール輸送層、発光層、電子輸送層、電子注入層、及びカソードを連続して積層してなる有機電界発光装置における発光層ドーパントとして用いられる赤色リン光物質に関する。   The present invention relates to an organic electroluminescent device, and more particularly to a red phosphorescent compound and an organic electroluminescent device using the same. More specifically, the present invention is used as a light emitting layer dopant in an organic electroluminescent device in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially stacked. Related to the red phosphor.

近年、表示装置の大型化が進むに伴い、省スペースを図ることのできるフラット表示装置への需要が高まりつつある。この種のフラット表示装置は、有機発光ダイオード（ＯＬＥＤ）と呼ばれる有機電界発光装置を含む。この有機電界発光装置の製作技術の進展には目を見張るものがあり、既に種々の試作品が上市されている。   In recent years, as the size of display devices increases, the demand for flat display devices that can save space is increasing. This type of flat display device includes an organic electroluminescent device called an organic light emitting diode (OLED). The progress of this organic electroluminescence device manufacturing technology is remarkable, and various prototypes are already on the market.

有機電界発光装置においては、電子注入電極（カソード）とホール注入電極（アノード）との間に設けられている有機層内に電荷が注入されるときに発光する。より具体的に、１つの電子と１つのホールが対をなし、このようにして得られた電子及びホールの対が崩壊するときに光が発せられる。有機電界発光装置は、プラスチックなどの可撓性の透明基板の上に形成可能である。有機電界発光装置は、プラズマ表示パネルまたは無機電界発光（ＥＬ）表示に求められる電圧よりも低い電圧（すなわち、１０Ｖの電圧またはそれ以下の電圧）下で駆動可能である。有機電界発光装置は、他の表示装置に比べてエネルギー消耗がより低く、色表現性に優れているというメリットがある。さらに、有機電界発光装置は３色（すなわち、緑色、青色、及び赤色）を用いて画像を再生することができることから、鮮明な画像が再生可能な次世代のカラー表示装置として幅広く認識されている。   In an organic electroluminescent device, light is emitted when electric charge is injected into an organic layer provided between an electron injection electrode (cathode) and a hole injection electrode (anode). More specifically, one electron and one hole make a pair, and light is emitted when the electron-hole pair thus obtained collapses. The organic electroluminescent device can be formed on a flexible transparent substrate such as plastic. The organic electroluminescent device can be driven under a voltage lower than a voltage required for a plasma display panel or an inorganic electroluminescent (EL) display (that is, a voltage of 10 V or lower). The organic electroluminescent device has the advantages of lower energy consumption and superior color expression than other display devices. Furthermore, since the organic electroluminescent device can reproduce an image using three colors (that is, green, blue, and red), it is widely recognized as a next-generation color display device capable of reproducing a clear image. .

このような有機電界発光（ＥＬ）装置の製造方法について述べると、下記の通りである：
（１）アノード材料が透明基板上に塗布される。通常、インジウム錫酸化物（ＩＴＯ）がアノード材料として用いられる。 A method for manufacturing such an organic electroluminescence (EL) device is described as follows:
(1) An anode material is applied on a transparent substrate. Indium tin oxide (ITO) is usually used as the anode material.

（２）ホール注入層（ＨＩＬ）が前記アノード材料上に積層される。前記ホール注入層は、厚みが１０ｎｍ〜３０ｎｍの銅フタロシアニン（ＣｕＰｃ）層からなる。   (2) A hole injection layer (HIL) is laminated on the anode material. The hole injection layer is made of a copper phthalocyanine (CuPc) layer having a thickness of 10 nm to 30 nm.

（３）次いで、ホール輸送層（ＨＴＬ）が積層される。前記ホール輸送層は、主として、４，４’−ビス［Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ］−ビフェニル（ＮＰＢ）からなるが、この物質は、真空蒸発処理が施されてから３０ｎｍ〜６０ｎｍの厚みに塗布される。   (3) Next, a hole transport layer (HTL) is laminated. The hole transport layer is mainly composed of 4,4′-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl (NPB), which is 30 nm after being subjected to vacuum evaporation treatment. It is applied to a thickness of ˜60 nm.

（４）この後、有機発光層が設けられる。このとき、必要に応じて、ドーパントが添加される。緑色発光の場合、前記有機発光層は、通常、トリス（８−ヒドロキシ−キノレート）アルミニウム（Ａｌｑ３）から形成されるが、この物質には、厚みが３０ｎｍ〜６０ｎｍとなるように真空蒸発処理が施される。なお、Ｎ−メチルキナクリドン（ＭＱＤ）もまたドーパント（あるいは、不純物）として用いられる。 (4) Thereafter, an organic light emitting layer is provided. At this time, a dopant is added as necessary. In the case of green light emission, the organic light emitting layer is usually formed from tris (8-hydroxy-quinolate) aluminum (Alq 3 ), but this material is subjected to vacuum evaporation treatment so that the thickness is 30 nm to 60 nm. Applied. N-methylquinacridone (MQD) is also used as a dopant (or impurity).

（５）電子輸送層（ＥＴＬ）及び電子注入層（ＥＩＬ）が連続して前記有機発光層の上に設けられるか、あるいは、電子注入／輸送層が前記有機発光層の上に設けられる。緑色発光の場合、（４）のＡｌｑ３が卓越した電子輸送能を有している。このため、前記電子注入及び輸送層は必須なものではない。 (5) An electron transport layer (ETL) and an electron injection layer (EIL) are continuously provided on the organic light emitting layer, or an electron injection / transport layer is provided on the organic light emitting layer. In the case of green light emission, Alq 3 in (4) has an excellent electron transport ability. For this reason, the electron injection and transport layer is not essential.

（６）最後に、カソード層が塗布され、保護層が前記全体構造物の上に塗布される。   (6) Finally, a cathode layer is applied and a protective layer is applied over the entire structure.

青色、緑色、及び赤色をそれぞれ発色する発光装置は、上述した構造物内における発光層の形成方法によって決められる。発光物質としてのエキシトンは、それぞれの電極から注入される電子とホールとの再組合せにより形成される。一重項エキシトンは蛍光を発し、三重項エキシトンはリン光を発する。蛍光を発する前記一重項エキシトンが形成される確率は約２５％であるが、リン光を発する三重項エキシトンが形成される確率は７５％となる。このため、三重項エキシトンは一重項エキシトンに比べて発光効率がさらに高い。これらのリン光物質のうち赤色リン光物質は、蛍光物質よりも発光効率がさらに高いことがある。この理由から、赤色リン光物質が有機電界発光装置の効率を高めるための重要な因子として研究及び調査されている。   The light emitting device that develops blue, green, and red colors is determined by the method for forming the light emitting layer in the structure. Exciton as a luminescent material is formed by recombination of electrons and holes injected from each electrode. Singlet excitons emit fluorescence and triplet excitons emit phosphorescence. The probability that the singlet excitons that emit fluorescence are formed is about 25%, but the probability that triplet excitons that emit phosphorescence are formed is 75%. For this reason, triplet excitons have higher luminous efficiency than singlet excitons. Of these phosphors, red phosphors may have higher luminous efficiency than fluorescent materials. For this reason, red phosphors have been studied and investigated as important factors for increasing the efficiency of organic electroluminescent devices.

このようなリン光物質を用いる場合、高発光効率、高色純度及びより強い耐久力が求められる。特に、赤色リン光物質を用いる場合、色純度が上がるにつれて、すなわち、ＣＩＥ色座標のＸ値が高くなるにつれて可視度が下がるため、高発光効率を得るには難点がある。この理由から、優れた色座標（ＣＩＥ色純度がＸ＝０．６５以上である。）、向上した発光効率、及びより強い耐久力の特性が得られる赤色リン光物質の開発がが望まれている。   When such a phosphorescent material is used, high luminous efficiency, high color purity, and stronger durability are required. In particular, when a red phosphorescent substance is used, the visibility decreases as the color purity increases, that is, as the X value of the CIE color coordinate increases, so that there is a difficulty in obtaining high luminous efficiency. For this reason, it is desired to develop a red phosphor that provides excellent color coordinates (CIE color purity is X = 0.65 or more), improved luminous efficiency, and stronger durability. Yes.

本発明は上記事情に鑑みてなされたものであり、その目的は、関連技術の限界及び欠点による１以上の問題点を実質的になくす赤色リン光化合物及びこれを用いた有機電界発光装置を提供するところにある。   The present invention has been made in view of the above circumstances, and an object thereof is to provide a red phosphorescent compound that substantially eliminates one or more problems due to limitations and disadvantages of related technology and an organic electroluminescence device using the same. There is a place to do.

本発明の他の目的は、有機電界発光装置における発光層ドーパントとして用いられる、下記の一般式１で表わされる化合物を化合することにより、色純度及び輝度が高く、しかも、耐久性の強い有機電界発光装置を提供するところにある。   Another object of the present invention is to combine a compound represented by the following general formula 1, which is used as a light emitting layer dopant in an organic electroluminescent device, to achieve an organic electric field having high color purity and high brightness and high durability. A light-emitting device is provided.

本発明の上記の目的は、下記の一般式１で表わされる赤色リン光化合物を提供することにより達成することができる：   The above object of the present invention can be achieved by providing a red phosphorescent compound represented by the following general formula 1:

を示すが、ここで、Ｒ１、Ｒ２、Ｒ３、及びＲ４は、それぞれ互いに独立して置換または非置換されたＣ１〜Ｃ６のアルキル基のうちいずれか１種であってもよい。また、Ｃ１〜Ｃ６のアルキル基は、それぞれメチル、エチル、ｎ−プロピル，ｉ−プロピル，ｎ−ブチル、ｉ−ブチル、及びｔ−ブチルからなる群から選択されてもよい。さらに、 Here, R1, R2, R3, and R4 may be any one of C1-C6 alkyl groups each independently substituted or unsubstituted. The C1-C6 alkyl group may be selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, and t-butyl, respectively. further,

は、 Is

を含んでいてもよい。なお、 May be included. In addition,

は、下記の一般式で表わされるいずれか１種であってもよい。： May be any one of the following general formulas. :

また、上記の一般式１は、下記の一般式のいずれかであってもよい。： The general formula 1 may be any of the following general formulas. :

本発明の他の態様によれば、互いに連続して積層されたアノード、ホール注入層、ホール輸送層、発光層、電子輸送層、電子注入層、及びカソードを備える有機電界発光装置が提供されるが、前記有機電界発光装置は、上記の一般式で表わされるいずれかを発光層ドーパントとして用いることができる。 According to another aspect of the present invention, there is provided an organic electroluminescent device comprising an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode that are successively stacked. However, the organic electroluminescent device can use any one of the above general formulas as a light emitting layer dopant.

この理由から、Ａｌ金属錯体とＺｎ金属錯体とカルバゾール誘導体のうちいずれか1種が発光層ホストとして使用可能であり、前記ドーパントは０．１ｗｔ％〜５０ｗｔ％の範囲内の量にて使用可能である。本発明は、ドーパントの使用量が上述の範囲内に収まるときに限って有効である。さらに、Ａｌ金属錯体及びＺｎ金属錯体それぞれのリガンドはキノリル、ビフェニル、イソキノリル、フェニル、メチルキノリル、ジメチル−キノリル、ジメチル−イソキノリルを含んでいてもよく、前記カルバゾール誘導体はＣＢＰを含んでいてもよい。 For this reason, is any one of a Al metal complex and Zn metal complex thereof and a carbazole derivative is usable as a light emitting layer host, the dopant is available in an amount in the range of 0.1 wt% 50 wt% It is. The present invention is effective only when the amount of dopant used falls within the above-mentioned range. Furthermore, Al metal complexes and Zn metal complex bodies each ligand quinolyl, biphenyl, isoquinolyl, phenyl, Mechirukinoriru, dimethyl - quinolyl, dimethyl - may contain isoquinolyl, wherein the carbazole derivative may include CBP.

以下、本発明の好適な具体例について詳述するが、これらの例示は添付図面に示してある。   Hereinafter, preferred specific examples of the present invention will be described in detail, and these examples are shown in the accompanying drawings.

以下、本発明による赤色リン光化合物を化合させる方法について説明する。本発明の有機電界発光装置に用いられる赤色リン光化合物のうち、イリジウム（ＩＩＩ）（２−（３−メチルフェニル）−７−メチル−キノリナト−Ｎ、Ｃ２）（２，４−ペンタンジオナート−０，０）化合物は、Ａ−２で表わされる。 Hereinafter, a method of combining the red phosphorescent compound according to the present invention will be described. Of the red phosphorescent compounds used in the organic electroluminescent device of the present invention, iridium (III) (2- (3-methylphenyl) -7-methyl-quinolinato-N, C 2 ) (2,4-pentanedionate) The (−0,0) compound is represented by A-2.

化合例
１．２−（３−メチルフェニル）−６−メチル−キノリンの製造 Compound Example 1.2 Production of 2- (3-methylphenyl) -6-methyl-quinoline

３−メチル−フェニル−ホウ酸（１．３ｍｍｏｌ）、２−クロロ−６−メチル−キノリン（１ｍｍｏｌ）、テトラキス（トリフェニルホスフィン）パラジウム（０）（０．０５ｍｍｏｌ）、及び炭酸カリウム（３ｍｍｏｌ）をＴＨＦ（３０ｍｌ）とＨ２Ｏ（１０ｍｌ）を含有する２口丸フラスコ中において溶解させる。この後、前記混合物を１００℃の浴中において２４時間かけて攪拌する。次いで、反応がそれ以上起こらないとき、前記ＴＨＦとトルエンを放棄する。ジクロロメタンと水を用いて前記混合物を抽出した後、真空蒸留処理を施す。この後、シリカゲルカラムにより前記混合物をろ過した後、溶媒を真空蒸留処理して除去する。その後、ジクロロメタンとペトローリアムエーテルを用いて前記混合物を再結晶化した後、ろ過して２−（３−メチルフェニル）−６−メチル−キノリン個体を得る。 3-methyl-phenyl-boric acid (1.3 mmol), 2-chloro-6-methyl-quinoline (1 mmol), tetrakis (triphenylphosphine) palladium (0) (0.05 mmol), and potassium carbonate (3 mmol). Dissolve in a two-necked round flask containing THF (30 ml) and H 2 O (10 ml). After this, the mixture is stirred in a 100 ° C. bath for 24 hours. The THF and toluene are then discarded when no further reaction takes place. The mixture is extracted with dichloromethane and water and then subjected to vacuum distillation. Thereafter, the mixture is filtered through a silica gel column, and then the solvent is removed by vacuum distillation. Thereafter, the mixture is recrystallized using dichloromethane and petroleum ether and filtered to obtain a 2- (3-methylphenyl) -6-methyl-quinoline solid.

２．塩素橋架された異合体錯物の形成   2. Formation of heterogeneous complex with chlorine bridge

塩化イリジウム（１ｍｍｏｌ）と２−（３−メチルフェニル）−６−メチル−キノリン（２．５ｍｍｏｌ）を２−エトキシエタノールと蒸留水との３：１液相混合物（３０ｍｌ）中において混合する。それから、前記混合物を２４時間かけて還流させる。この後、生成物を個形にろ過するために水を加える。次いで、メタノールとペトローリアムエーテルを用いて前記個体を洗浄することにより、塩素橋架された異合体錯物を得る。 Iridium chloride (1 mmol) and 2- (3-methylphenyl) -6-methyl-quinoline (2.5 mmol) are mixed in a 3: 1 liquid phase mixture (30 ml) of 2-ethoxyethanol and distilled water. The mixture is then refluxed for 24 hours. After this, water is added to filter the product into a solid. Subsequently, the said solid body is wash | cleaned using methanol and petrolium ether, and the heterozygote complex bridge | crosslinked with chlorine is obtained.

３．イリジウム（ＩＩＩ）（２−（３−メチルフェニル）−６−メチル−キノリナト−Ｎ、Ｃ２）（２，４−ペンタンジオナート−０，０）の形成 3. Formation of iridium (III) (2- (3-methylphenyl) -6-methyl-quinolinato-N, C 2 ) (2,4-pentanedionate-0,0)

前記塩素橋架された二量体錯物（１ｍｍｏｌ）、２，４−ペンタンジオン（３ｍｍｏｌ）、及びＮａ２ＣＯ３（６ｍｍｏｌ）を２−エトキシエタノール（３０ｍｌ）中において混合した後、２４時間かけて還流させる。前記還流された混合物を室温下で冷却させる。この後、蒸留水を前記冷却された混合物に加えた後、ろ過して個体生成物を得る。次いで、前記個体生成物をジクロロメタンに溶解させた後、シリカゲルを用いてろ過する。この後、前記ジクロロメタンを真空吸入処理し、前記固体をメタノール及びペトローリアムエーテルにより洗浄して前記化合物を得る。 The chlorine-bridged dimer complex (1 mmol), 2,4-pentanedione (3 mmol), and Na 2 CO 3 (6 mmol) were mixed in 2-ethoxyethanol (30 ml), and then over 24 hours. Reflux. The refluxed mixture is allowed to cool at room temperature. Thereafter, distilled water is added to the cooled mixture, followed by filtration to obtain a solid product. Next, the solid product is dissolved in dichloromethane and filtered using silica gel. Thereafter, the dichloromethane is subjected to vacuum suction treatment, and the solid is washed with methanol and petroleum ether to obtain the compound.

以下、本発明を説明するための好適な具体例を挙げるが、本発明はこれらの具体例に限定されるものではない。   Hereinafter, preferred specific examples for explaining the present invention will be described, but the present invention is not limited to these specific examples.

具体例
１．第１の具体例
ＩＴＯガラス基板は３ｍｍ×３ｍｍの発光面積を有するようにパターニングされる。それから、前記パターニングされたＩＴＯガラス基板は洗浄される。次いで、前記基板は真空チャンバーに載置され、その標準圧は１×１０−６ｔｏｒｒに設定される。この後、有機物層はＣｕＰＣ（２００Å）、ＮＰＢ（４００Å）、ＢＡｌｑ＋Ａ−２（７％）（２００Å）、Ａｌｑ３（３００Å）、ＬｉＦ（５Å）及びＡｌ（１０００Å）の順に前記ＩＴＯ基板の上に形成される。 Specific example 1. First Specific Example The ITO glass substrate is patterned to have a light emitting area of 3 mm × 3 mm. Then, the patterned ITO glass substrate is cleaned. Next, the substrate is placed in a vacuum chamber, and its standard pressure is set to 1 × 10 −6 torr. Thereafter, the organic layer is formed on the ITO substrate in the order of CuPC (200Å), NPB (400Å), BAlq + A-2 (7%) (200Å), Alq 3 (300Å), LiF (5Å) and Al (1000Å). It is formed.

０．９ｍＡにおける輝度は１０６６ ｃｄ／ｍ２（６．５Ｖ）であり、このとき、ＣＩＥｘ＝０．６４６、ｙ＝０．３５１である。なお、耐久性（初期輝度の半分値）は２０００ｃｄ／ｍ２において５５００時間持続される。 The luminance at 0.9 mA is 1066 cd / m 2 (6.5 V). At this time, CIEx = 0.646 and y = 0.351. The durability (half value of the initial luminance) is maintained for 5500 hours at 2000 cd / m 2 .

２．第２の具体例
ＩＴＯガラス基板は３ｍｍ×３ｍｍの発光面積を有するようにパターニングされる。それから、前記パターニングされたＩＴＯガラス基板は洗浄される。次いで、前記基板は真空チャンバーに載置され、その標準圧は１×１０−６ｔｏｒｒに設定される。この後、有機物層はＣｕＰＣ（２００Å）、ＮＰＢ（４００Å）、ＢＡｌｑ＋Ａ−７（７％）（２００Å）、Ａｌｑ３（３００Å）、ＬｉＦ（５Å）及びＡｌ（１０００Å）の順に前記ＩＴＯ基板の上に形成される。 2. Second Specific Example The ITO glass substrate is patterned to have a light emitting area of 3 mm × 3 mm. Then, the patterned ITO glass substrate is cleaned. Next, the substrate is placed in a vacuum chamber, and its standard pressure is set to 1 × 10 −6 torr. Thereafter, the organic layer is CuPC (200Å), NPB (400Å ), BAlq + A-7 (7%) (200Å), Alq 3 (300Å), on the ITO substrate in order of LiF (5 Å) and Al (1000 Å) It is formed.

０．９ｍＡにおける輝度は１１０２ｃｄ／ｍ２（６．１Ｖ）であり、このとき、ＣＩＥｘ＝０．６４５、ｙ＝０．３５２である。なお、耐久性（初期輝度の半分値）は２０００ｃｄ／ｍ２において５８００時間持続される。 The luminance at 0.9 mA is 1102 cd / m 2 (6.1 V), and at this time, CIEx = 0.645 and y = 0.352. The durability (half value of the initial luminance) lasts for 5800 hours at 2000 cd / m 2 .

３．第３の具体例
ＩＴＯガラス基板は３ｍｍ×３ｍｍの発光面積を有するようにパターニングされる。それから、前記パターニングされたＩＴＯガラス基板は洗浄される。次いで、前記基板は真空チャンバーに載置され、その標準圧は１×１０−６ｔｏｒｒに設定される。この後、有機物層はＣｕＰＣ（２００Å）、ＮＰＢ（４００Å）、ＢＡｌｑ＋Ａ−９（７％）（２００Å）、Ａｌｑ３（３００Å）、ＬｉＦ（５Å）及びＡｌ（１０００Å）の順に前記ＩＴＯ基板の上に形成される。 3. Third Specific Example The ITO glass substrate is patterned to have a light emitting area of 3 mm × 3 mm. Then, the patterned ITO glass substrate is cleaned. Next, the substrate is placed in a vacuum chamber, and its standard pressure is set to 1 × 10 −6 torr. Thereafter, the organic layer is CuPC (200Å), NPB (400Å ), BAlq + A-9 (7%) (200Å), Alq 3 (300Å), on the ITO substrate in order of LiF (5 Å) and Al (1000 Å) It is formed.

０．９ｍＡにおける輝度は９４９ｃｄ／ｍ２（５．３Ｖ）であり、このとき、ＣＩＥｘ＝０．６５８、ｙ＝０．３３９である。なお、耐久性（初期輝度の半分値）は２０００ｃｄ／ｍ２において５０００時間持続される。 The luminance at 0.9 mA is 949 cd / m 2 (5.3 V), and at this time, CIEx = 0.658 and y = 0.339. The durability (half value of the initial luminance) lasts 5000 hours at 2000 cd / m 2 .

４．第４の具体例
ＩＴＯガラス基板は３ｍｍ×３ｍｍの発光面積を有するようにパターニングされる。それから、前記パターニングされたＩＴＯガラス基板は洗浄される。次いで、前記基板は真空チャンバーに載置され、その標準圧は１×１０−６ｔｏｒｒに設定される。この後、有機物層はＣｕＰＣ（２００Å）、ＮＰＢ（４００Å）、ＣＢＰ＋Ａ−２（７％）（２００Å）、Ａｌｑ３（３００Å）、ＬｉＦ（５Å）及びＡｌ（１０００Å）の順に前記ＩＴＯ基板の上に形成される。 4). Fourth Specific Example The ITO glass substrate is patterned to have a light emitting area of 3 mm × 3 mm. Then, the patterned ITO glass substrate is cleaned. Next, the substrate is placed in a vacuum chamber, and its standard pressure is set to 1 × 10 −6 torr. Thereafter, the organic layer is formed on the ITO substrate in the order of CuPC (200Å), NPB (400Å), CBP + A-2 (7%) (200Å), Alq 3 (300Å), LiF (5Å), and Al (1000Å). It is formed.

ＢＡｌｑを用いてホール保持層を設ける場合、０．９ｍＡにおける輝度は９８６ｃｄ／ｍ２（５．３Ｖ）であり、このとき、ＣＩＥｘ＝０．６４１、ｙ＝０．３５７である。なお、耐久性（初期輝度の半分値）は２０００ｃｄ／ｍ２において４５００時間持続される。 When the hole holding layer is provided using BAlq, the luminance at 0.9 mA is 986 cd / m 2 (5.3 V), and at this time, CIE x = 0.641 and y = 0.357. The durability (half value of the initial luminance) lasts for 4500 hours at 2000 cd / m 2 .

比較例
ＩＴＯガラス基板は３ｍｍ×３ｍｍの発光面積を有するようにパターニングされる。それから、前記パターニングされたＩＴＯガラス基板は洗浄される。次いで、前記基板は真空チャンバーに載置され、その標準圧は１×１０−６ｔｏｒｒに設定される。この後、有機物層はＣｕＰｃ（２００Å）、ＮＰＢ（４００Å）、ＢＡｌｑ＋（ｂｔｐ）２Ｉｒ（ａｃａｃ）（７％）（２００Å）、Ａｌｑ３（３００Å）、ＬｉＦ（５Å）、及びＡｌ（１０００Å）の順に前記ＩＴＯ基板の上に形成される。 Comparative Example The ITO glass substrate is patterned to have a light emitting area of 3 mm × 3 mm. Then, the patterned ITO glass substrate is cleaned. Next, the substrate is placed in a vacuum chamber, and its standard pressure is set to 1 × 10 −6 torr. After this, the organic layer is composed of CuPc (200Å), NPB (400Å), BAlq + (btp) 2 Ir (acac) (7%) (200Å), Alq 3 (300Å), LiF (5Å), and Al (1000Å). In order, it is formed on the ITO substrate.

０．９ｍＡにおける輝度は７８０ｃｄ／ｍ２（７．５Ｖ）であり、このとき、ＣＩＥｘ＝０．６５９、ｙ＝０．３２９である。なお、耐久性（初期輝度の半分値）は２０００ｃｄ／ｍ２において２５００時間持続される。 The luminance at 0.9 mA is 780 cd / m 2 (7.5 V), and at this time, CIEx = 0.659 and y = 0.329. The durability (half value of the initial luminance) lasts 2500 hours at 2000 cd / m 2 .

上述した具体例と比較例の効率、色座標、輝度、及び耐久性の特性を下記表１に示す。   The efficiency, color coordinates, luminance, and durability characteristics of the specific examples and comparative examples described above are shown in Table 1 below.

上記表１に示すように、前記装置は色純度が高い場合であっても（ＣＩＥ（Ｘ）≧０．６５）、低電圧において高効率にて作動する。さらに、前記第２の具体例の電流効率は前記比較例に比べて７０％以上高くなっている。なお、前記第２の具体例の耐久性は前記比較例のそれよりも２倍ほど高くなっている。 As shown in Table 1 above, the device operates with high efficiency at low voltage even when the color purity is high (CIE (X) ≧ 0.65). Furthermore, the current efficiency of the second specific example is 70% or more higher than that of the comparative example. The durability of the second specific example is twice as high as that of the comparative example.

下記表２は、本発明の第２の具体例による有機電界発光装置における、電圧及び電流の増加による効率、色座標、及び輝度の特性を示す。   Table 2 below shows characteristics of efficiency, color coordinates, and luminance due to increase in voltage and current in the organic electroluminescent device according to the second specific example of the present invention.

上記表２に示すように、前記第２の具体例によれば、優れた効率が得られ、しかも、駆動電圧による色座標も高い色純度を維持している。 As shown in Table 2 above, according to the second specific example, excellent efficiency can be obtained, and the color coordinates based on the drive voltage maintain high color purity.

本発明の趣旨及び範疇から逸脱しない限り、種々の応用及び変形が可能であることは当業者にとって自明である。よって、これらの応用及び変形が特許請求の範囲に属することは当然なことである。   It will be apparent to those skilled in the art that various modifications and variations can be made without departing from the spirit and scope of the invention. Therefore, it is natural that these applications and modifications belong to the scope of claims.

上記一般式１で表わされる化合物を前記有機電界発光装置の発光層として用いることにより、本発明は色純度及び輝度に優れ、しかも、耐久性が強くなる有機電界発光装置を提供することが可能になる。   By using the compound represented by the above general formula 1 as the light emitting layer of the organic electroluminescent device, the present invention can provide an organic electroluminescent device that is excellent in color purity and luminance and has high durability. Become.

本発明への理解を容易にするための提供される添付図面は本発明の具体例を開示しており、本発明の内容と共に本発明の原理を説明するものである。
有機電界発光装置の色純度が上がるに伴い、すなわち、色座標のＸ値が高くなるに伴い可視度が下がる様子を示すグラフである。 本発明の具体例において用いられる化合物としてのＮＰＢ、銅（ＩＩ）フタロシアニン（ＣｕＰｃ）、（ｂｐｔ）２Ｉｒ（ａｃａｃ）、Ａｌｑ３、ＢＡｌｑ、及びＣＢＰの構造式を示す。 The accompanying drawings provided for facilitating the understanding of the present invention disclose specific examples of the present invention and explain the principle of the present invention together with the contents of the present invention.
It is a graph which shows a mode that a visibility falls, as the color purity of an organic electroluminescent apparatus goes up, ie, the X value of a color coordinate becomes high. The structural formulas of NPB, copper (II) phthalocyanine (CuPc), (bpt) 2 Ir (acac), Alq 3 , BAl q , and CBP as compounds used in the specific examples of the present invention are shown.

Claims (8)

下記の化学式１で表わされる赤色リン光化合物であって、：
を示し、
Ｒ１、Ｒ２、Ｒ３、及びＲ４はそれぞれ互いに独立してＨ、または置換もしくは非置換のＣ１〜Ｃ６アルキル基から選択され、
そして、
は、２，４−ペンタンジオン、２，２，６，６−テトラ−メチルヘプタン−３，５−ジオン、１，３−プロパンジオン、１，３−ブタンジオン、３，５−ヘプタンジオン、１，１，１−トリフルオロ−２，４−ペンタンジオン、１，１，１，５，５，５−ヘキサフルオロ−２，４−ペンタンジオン、及び２，２−ジメチル−３，５−ヘキサンジオンからなる群から選択されるアルカンジオンを示す、赤色リン光化合物。A red phosphorescent compound represented by Chemical Formula 1 below:
Indicate
R1, R2, R3, and R4 are each independently selected from H or a substituted or unsubstituted C1-C6 alkyl group;
And
Is 2,4-pentanedione, 2,2,6,6-tetra-methylheptane-3,5-dione, 1,3-propanedione, 1,3-butanedione, 3,5-heptanedione, 1, From 1,1-trifluoro-2,4-pentanedione, 1,1,1,5,5,5-hexafluoro-2,4-pentanedione, and 2,2-dimethyl-3,5-hexanedione A red phosphorescent compound showing an alkanedione selected from the group consisting of: 前記Ｃ１〜Ｃ６アルキル基はそれぞれメチル、エチル、ｎ−プロピル、ｉ−プロピル、ｎ−ブチル、ｉ−ブチル、及びｔ−ブチルからなる群から選ばれるいずれか１種である請求項１に記載の赤色リン光化合物。  2. The C1-C6 alkyl group is any one selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, and t-butyl. Red phosphorescent compound. は、下記の化学式で表わされるもののうちいずれか１種である請求項１に記載の赤色リン光化合物：
 The red phosphorescent compound according to claim 1, wherein is one of those represented by the following chemical formula:
前記化学式１は、下記の化学式のうちいずれか１つである請求項１に記載の赤色リン光化合物：
The red phosphorescent compound according to claim 1, wherein the chemical formula 1 is any one of the following chemical formulas:
発光層を備える有機電界発光装置であって、該発光層は、下記の式１で表わされる赤色リン光化合物をドーパントとして含み：
を示し、
Ｒ１、Ｒ２、Ｒ３、及びＲ４はそれぞれ互いに独立してＨ、または置換もしくは非置換のＣ１〜Ｃ６アルキル基から選択され、
そして、
は、２，４−ペンタンジオン、２，２，６，６−テトラ−メチルヘプタン−３，５−ジオン、１，３−プロパンジオン、１，３−ブタンジオン、３，５−ヘプタンジオン、１，１，１−トリフルオロ−２，４−ペンタンジオン、１，１，１，５，５，５−ヘキサフルオロ−２，４−ペンタンジオン、及び２，２−ジメチル−３，５−ヘキサンジオンからなる群から選択されるアルカンジオンを示す、有機電界発光装置。An organic electroluminescent device comprising a light emitting layer, wherein the light emitting layer contains a red phosphorescent compound represented by the following formula 1 as a dopant:
Indicate
R1, R2, R3, and R4 are each independently selected from H or a substituted or unsubstituted C1-C6 alkyl group;
And
Is 2,4-pentanedione, 2,2,6,6-tetra-methylheptane-3,5-dione, 1,3-propanedione, 1,3-butanedione, 3,5-heptanedione, 1, From 1,1-trifluoro-2,4-pentanedione, 1,1,1,5,5,5-hexafluoro-2,4-pentanedione, and 2,2-dimethyl-3,5-hexanedione An organic electroluminescent device showing an alkanedione selected from the group consisting of: Ａｌ金属錯体とＺｎ金属錯体とカルバゾール誘導体のうちいずれか一つを発光層のホストとして用いる請求項５に記載の有機電界発光装置。  The organic electroluminescent device according to claim 5, wherein any one of an Al metal complex, a Zn metal complex, and a carbazole derivative is used as a host of the light emitting layer. Ａｌ金属錯体とＺｎ金属錯体とカルバゾール誘導体のうちいずれか一つを発光層のホストとして用い、前記ドーパントの使用量は、前記ドーパントを含む発光層の重量に全体として基づいて、０．１〜５０ｗｔ％の範囲を有する請求項５に記載の有機電界発光装置。  Any one of an Al metal complex, a Zn metal complex, and a carbazole derivative is used as a host of the light emitting layer, and the amount of the dopant used is 0.1 to 50 wt based on the weight of the light emitting layer including the dopant as a whole. The organic electroluminescent device according to claim 5 having a range of%. Ａｌ金属錯体及びＺｎ金属錯体のそれぞれのリガンドはキノリル、ビフェニル、イソキノリル、フェニル、メチルキノリル、ジメチル−キノリルまたはジメチル−イソキノリルを含み、カルバゾール誘導体はＣＢＰを含む請求項６に記載の有機電界発光装置。The organic electroluminescent device according to claim 6, wherein each of the ligands of the Al metal complex and the Zn metal complex includes quinolyl, biphenyl, isoquinolyl, phenyl, methylquinolyl, dimethyl-quinolyl or dimethyl-isoquinolyl , and the carbazole derivative includes CBP.
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